Acetic Acid → HCID 49847808, compound

HRID 389861Notes

Reaction equation

HRID 389861 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C@@H:11]2[CH2:14][CH2:13][NH:12]2)=[O:10])=[N:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2].Cl.[O:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C(O)(=O)C.C([BH3-])#N>C1COCC1>[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C@@H:11]2[CH2:14][CH2:13][N:12]2[CH2:28][CH:25]2[CH2:26][CH2:27][O:22][CH2:23][CH2:24]2)=[O:10])=[N:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 498716Cyano-borohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 86665998HCID 86665998, compound

Product 1

HCID 49847808HCID 49847808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-Azetidine-2-carboxylic acid (5-ethyl-4-phenyl-thiazol-2-yl)-amide; hydrochloride (100 mg; 0.309 mmol) in THF (1.5 mL) id added tetrahydro-pyran-4-carbaldehyde (70.5 mg; 0.618 mmol), acetic acid (0.071 mL; 1.236 mmol) and MP-cyanoborohydride (327 mg; 2.36 mmol/g). The reaction mixture is agitated at room temperature for 18 hours. After this time, the reaction mixture is filtered and the filtrate is washed with saturated sodium bicarbonate aqueous solution then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 386 [M+H+].

Workup

  1. filtrationAfter this time, the reaction mixture is filtered
  2. washthe filtrate is washed with saturated sodium bicarbonate aqueous solution
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5885df3ab8034b7ea40cabacd48cbbdb
Source dataset
uspto-grants-2013_02
Patent number
US08383615B2

Reaction notes

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